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Jeroen D C Codée

Publications and source records attributed to Jeroen D C Codée.

10 recordsLinked to original sources
PubMed2006

Microreactors as tools for synthetic chemists-the chemists' round-bottomed flask of the 21st century?

Will microreactors replace the round-bottomed flask to perform chemical reactions in the near future? Recent developments in the construction of microstructured reaction devices and their wide-ranging applications in many different areas of chemistry suggest that they can have a significant impact on the way chemists conduct their experiments. Miniaturizing reactions offers many advantages for the synthetic organic chemist: high-throughput scanning of reaction conditions, precise control of reaction variables, the use of small quantities of reagents, increased safety parameters, and ready scale-up of synthetic procedures. A wide range of single- and multiphase reactions have now been performed in microfluidic-based devices. Certainly, microreactors cannot be applied to all chemistries yet and microfluidic systems also have disadvantages. Limited reaction-time range, high sensitivity to precipitating products, and new physical, chemical, and analytical challenges have to be overcome. This concept article presents an overview of microfluidic devices available for chemical synthesis and evaluates the potential of microreactor technology in organic synthesis.

Journal Article↗
PubMed2005

Thioglycosides in sequential glycosylation strategies.

This tutorial review surveys the use of thioglycosides in the development of sequential glycosylation methodologies, with a focus on chemoselective, orthogonal and iterative glycosylation strategies reported since the beginning of this century. Both fundamental aspects of glycosidic bond formation and ingenious state-of-the-art methodologies are presented.

Amino Acids↗
PubMed2005

Efficient installation of beta-mannosides using a dehydrative coupling strategy.

[reaction: see text]. A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.

Combinatorial Chemistry Techniques↗
PubMed2005

A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy.

A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.

Carbohydrate Sequence↗
PubMed2004

Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.

[reaction: see text] Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

Cyclic N-Oxides↗
PubMed2003

A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides.

A tethered nucleophilic substitution strategy for the stereoselective introduction of axially oriented amino functions on suitably protected gluco- and mannopyranosides is presented. The obtained oxazine is a versatile building block, which after some manipulation, could be used in the construction of highly functionalised oligosaccharides.

Aminoglycosides↗
PubMed2003

Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.

[reaction: see text] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph(2)SO/Tf(2)O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.

Carbohydrate Sequence↗
PubMed2003

Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed. [reaction: see text]

Anhydrides↗